N[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=3)[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[F:20][C:21]([F:27])([F:26])[S:22](O)(=[O:24])=[O:23].N([O-])=O.[Na+]>CN(C)C=O>[F:20][C:21]([F:27])([F:26])[S:22]([C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=3)[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2)(=[O:24])=[O:23]To a solution of 6-amino-8-(3-cyanophenyl)-1,7-naphthyridine (4.058 g) in dimethyl-formamide (DMF) (22 ml) under argon at 0° C. is added trifluoromethanesulfonic acid (11 ml). The mixture is stirred at 0° C. for 10 minutes and then sodium nitrite (2.26 g) is added slowly. The cooling bath is then removed and the mixture stirred at room temperature for 3 hours. The resulting mixture is diluted with ethyl acetate and washed with water, 2M NaOH and water again. The organic layer is dried over sodium sulfate, then concentrated in vacuo and purified by column chromatography, eluting with 10:0.5 toluene:acetone to yield the title compound. M.p. 102-104° C. MS (m/e)=380.
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